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Jamf, the Apple device management company, filed to go public today. Jamf might not be a household name, but the Minnesota company has been around since 2002 helping companies manage their Apple equipment.

In the early days, that was Apple computers. Later it expanded to also manage iPhones and iPads. The company launched at a time when most IT pros had few choices for managing Macs in a business setting.

Jamf changed that, and as Macs and other Apple devices grew in popularity inside organizations in the 2010s, the company’s offerings grew in demand. Notably, over the years Apple has helped Jamf and its rivals considerably, by building more sophisticated tooling at the operating system level to help manage Macs and other Apple devices inside organizations.

Jamf raised approximately $50 million of disclosed funding before being acquired by Vista Equity Partners in 2017 for $733.8 million, according to the S-1 filing. Today, the company kicks off the high-profile portion of its journey toward going public.

Apple device management takes center stage

In a case of interesting timing, Jamf is filing to go public less than a week after Apple bought mobile device management startup Fleetsmith. At the time, Apple indicated that it would continue to partner with Jamf as before, but with its own growing set of internal tooling, which could at some point begin to compete more rigorously with the market leader.

Other companies in the space managing Apple devices besides Jamf and Fleetsmith include Addigy and Kandji. Other more general offerings in the mobile device management (MDM) space include MobileIron and VMware Airwatch among others.

Vista is a private equity shop with a specific thesis around buying out SaaS and other enterprise companies, growing them, and then exiting them onto the public markets or getting them acquired by strategic buyers. Examples include Ping Identity, which the firm bought in 2016 before taking it public last year, and Marketo, which Vista bought in 2016 for $1.8 billion and sold to Adobe last year for $4.8 billion, turning a tidy profit.

Inside the machine

Now that we know where Jamf sits in the market, let’s talk about it from a purely financial perspective.

Jamf is a modern software company, meaning that it sells its digital services on a recurring basis. In the first quarter of 2020, for example, about 83% of its revenue came from subscription software. The rest was generated by services and software licenses.

Now that we know what type of company Jamf is, let’s explore its growth, profitability and cash generation. Once we understand those facets of its results, we’ll be able to understand what it might be worth and if its IPO appears to be on solid footing.

We’ll start with growth. In 2018 Jamf recorded $146.6 million in revenue, which grew to $204.0 million in 2019. That works out to an annual growth rate of 39.2%, a more than reasonable pace of growth for a company going public. It’s not super quick, mind, but it’s not slow either. More recently, the company grew 36.9% from $44.1 million in Q1 2019 to $60.4 million in revenue in Q1 2020. That’s a bit slower, but not too much slower.

Turning to profitability, we need to start with the company’s gross margins. Then we’ll talk about its net margins. And, finally, adjusted profits.

Gross margins help us understand how valuable a company’s revenue is. The higher the gross margins, the better. SaaS companies like Jamf tend to have gross margins of 70% or above. In Jamf’s own case, it posted gross margins of 75.1% in Q1 2020, and 72.5% in 2019. Jamf’s gross margins sit comfortably in the realm of SaaS results, and, perhaps even more importantly, are improving over time.

Getting behind the curtain

When all its expenses are accounted for, the picture is less rosy, and Jamf is unprofitable. The company’s net losses for 2018 and 2019 were similar, totaling $36.3 million and $32.6 million, respectively. Jamf’s net loss improved a little in Q1, falling from $9.0 million in 2019 to $8.3 million this year.

The company remains weighed down by debt, however, which cost it nearly $5 million in Q1 2020, and $21.4 million for all of 2019. According to the S-1, Jamf is sporting a debt-to-equity ratio of roughly 0.8, which may be a bit higher than your average public SaaS company, and is almost certainly a function of the company’s buyout by a private equity firm.

But the company’s adjusted profit metrics strip out debt costs, and under the heavily massaged adjusted earnings before interest, taxes, depreciation and amortization (EBITDA) metric, Jamf’s history is only one of rising profitability. From $6.6 million in 2018 to $20.8 million in 2019, and from $4.3 million in Q1 2019 to $5.6 million in Q1 2020, with close to 10% adjusted operating profit margins through YE 2019.

It will be interesting to see how the company’s margins will be affected by COVID-19, with financials during the period still left blank in this initial version of the S-1. The Enterprise market in general has been reasonably resilient to the recent economic shock, and device management may actually perform above expectations, given the growing push for remote work.

Completing the picture

Something notable about Jamf is that it has positive cash generation, even if in Q1 it tends to consume cash that is made up for in other quarters. In 2019, the firm posted $11.2 million in operational cash flow. That’s a good result, and better than 2018’s $9.4 million of operating cash generation. (The company’s investing cash flows have often run negative due to Jamf acquiring other companies, like ZuluDesk and Digita.)

With Jamf, we have a SaaS company that is growing reasonably well, has solid, improving margins, non-terrifying losses, growing adjusted profits and what looks like a reasonable cash flow perspective. But Jamf is cash poor, with just $22.7 million in cash and equivalents as of the end of Q1 2020 — some months ago now. At that time, the firm also had debts of $201.6 million.

Given the company’s worth, that debt figure is not terrifying. But the company’s thin cash balance makes it a good IPO candidate; going public will raise a chunk of change for the company, giving it more operating latitude and also possibly a chance to lower its debt load. Indeed Jamf notes that it intends to use part of its IPO raise to “to repay outstanding borrowings under our term loan facility…” Paying back debt at IPO is common in private equity buyouts.

So what?

Jamf’s march to the public markets adds its name to a growing list of companies. The market is already preparing to ingest Lemonade and Accolade this week, and there are rumors of more SaaS companies in the wings, just waiting to go public.

There’s a reasonable chance that as COVID-19 continues to run roughshod over the United States, the public markets eventually lose some momentum. But that isn’t stopping companies like Jamf from rolling the dice and taking a chance going public.

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The pandemic has wreaked havoc on all manner of professional sports this year, and cycling has not been immune. For example, the best-known race on the planet, the Tour de France, normally staged in July, has had to be pushed back to August 29 through September 20.

That doesn’t mean that the world — and professional cyclists — can’t enjoy world-class racing this summer. In fact, beginning this coming weekend, 23 top men’s teams and 17 women’s teams will participate in a virtual version of the event that’s being hosted by six-year-old Zwift, after it was chosen by the official race organizer of the real tour, Amaury Sport Organization (ASO), as its partner on the event.

It’s a coup for the Long Beach, Calif., company whose multiplayer video game technology is used by both amateur and pro cyclists and that, according to Outside magazine, is now the biggest player in the growing online racing world.

Investors have noticed, funding the company to the tune of $170 million so far, says cofounder and CEO Eric Min.

This Tour has the potential to drive many more users its way, too.

For one thing, the virtual version of the event, which will feature six stages that last roughly hour over the next three weekends beginning this Saturday, will be broadcast in more than 130 countries. (The race gets underway with the first women’s stage, followed immediately by the men, and will be broadcast on NBC Sports here in the U.S.)

It’s hard to imagine another way for a company like Zwift to get so much exposure as quickly.

The race is also open to any cyclists on its platform who want to race on the same roads as the professionals, meaning anyone who wants to “compete” in this virtual tour needs to sign up for an account, though it’s worth noting a few things.

First, mere mortals won’t be racing at the same time as the cyclists in the Tour but during mass participation events during the week that will ostensibly provide them the chance to experience exactly what the pros went through and to compare their power, heart rate, cadence and other data to their pro rider heroes.

Also, Zwift is a subscription service. Users can check out the platform for a free, seven-day trial, but after that, Zwift charges $15 per month. Riders also need a smart trainer, which costs around $300. Zwift doesn’t make its own trainers — yet — but its software works with the hardware of a dozen or so companies.

Unsurprisingly, Min sounded both excited and terrified when we caught up with him last week to talk about the race, whose first two stages will be held in Zwift’s existing game world, Watopia, with the other stages orchestrated in virtual versions of real courses from the race.

Though Zwift has staged virtual races before —  including the Giro d’Italia, which is basically the Tour de France for Italy, and the Vuelta a Espana, an annual multi-stage race in Spain — it “doesn’t get any bigger than this,” said Min, who told us the idea was hatched six weeks ago with ASO and that Zwift has been working furiously to prepare for the race ever since.

It could prove a turning point for the outfit. It already has nearly two million accounts, and while subscribers ebb and flow, depending on the time of year, the virtual Tour is an opportunity for some of those riders to “reengage,” Min says, adding that Zwift has been growing 50 percent year over year, and has unsurprisingly seen pick-up accelerate throughout the pandemic.

Zwift doesn’t just cater to competitive athletes, Min stresses, saying that more than half the company’s customers are overweight and that, unlike Peleton, its customers are drawn less to particular instructors and more to the idea of being part of a club where they can train, take part in events, and compete with one another another, either in a public way or by via private rides wherein users share maps with friends, for example.

Either way, both amateur rider and professional racers will undoubtedly have high expectations of the Tour itself, even while it comes with more inherent challenges, including less time to break away from fellow riders than in the real-world tour, where each stage can take five or six hours.

Min thinks Zwift is ready. On our call, he discussed how Zwift convincingly creates drag, for example, walking through the software’s calculations, including a rider’s weight and body mass and the terrain they’re on and whether a rider is receiving draft from riders in front. Apply resistance to the machine  or easing it is what gives riders a sense of motion and inertia. “It’s not exactly like outdoor riding,” said Min, but combined with the software’s visual tools, meant to fool the mind, “it gets pretty darn close.

And that software, including the Tour maps, is now largely done, Min said. Now, Zwift just needs to ensure that its broadcast tools work as well as possible, among other last-minute priorities.

“We’ll do some dry runs [this] week. Then it’s showtime,” he said, before adding: “The stakes are pretty high. It has to be rock solid.”

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The Station is a weekly newsletter dedicated to all things transportation. Sign up here — just click The Station — to receive it every Saturday in your inbox.

Hi friends and first-time readers. Welcome back to The Station, a newsletter dedicated to all the present and future ways people and packages move from Point A to Point B. I’m your host Kirsten Korosec, senior transportation reporter at TechCrunch.

Remember please reach out and email me at kirsten.korosec@techcrunch.com to share thoughts, criticisms, offer up opinions or tips. You can also send a direct message to me at Twitter — @kirstenkorosec.

Typically this space is where I philosophize about a specific event and emerging transportation trend. This week, let’s all take a pause to remember Jessi Combs, who was officially and posthumously declared to hold the fastest land speed record by a woman.

The Guinness Book of World Records certified this week the 522.783 mph land speed record that Combs achieved August 27, 2019 in the Alvord Desert in Oregon. Combs died after her vehicle crashed during that run. It’s the first time a new record has been set in this category in more than 40 years. Kitty O’Neil held the record with her 512.7 mph run set back in 1976.

Here’s to you Jessi, the fastest woman on earth.

Did anyone have trouble keeping up with all the deals, virtual automotive reveals and policy decisions this week? Yeah. Me too. Let’s get to it. Vamos.

Micromobbin’

the station scooter1a

A couple of cities are emerging as new battlegrounds for the shared e-scooter market. New York City is a biggie.

This week, the New York City Council approved a bill that will require the New York Department of Transportation to create a pilot program for the operation of shared electric scooters in the city. The DOT now has until October 15, 2020 to issue a request for proposals to participate in a shared e-scooter pilot program.

The pilot program must launch by March 1, 2021. The NY council will continue to work with DOT on determining where to set up the pilot (this is the important part). If the pilot program limits the service area it could prove a failure, several e-scooter companies and advocates told me. We know it won’t include Manhattan. That leaves four other boroughs.

Just about every e-scooter company — and a number of other less known players — are planning to apply for the permit.  The next nine months promises a lot of lobbying activity. These firms are already busy, according to our sources. Stay tuned!

The NY city council also approved two laws about the use of privately owned electric bikes and scooters.

Meanwhile, Apple has finally added a new biking feature to Maps. The newest version of iOS is bringing a host of new features to Maps, including a dedicated cycling option that will optimize paths for bicyclists and even let users know if the route includes challenging hills. Apple Maps has included public transit and walking in previous iterations. But the biking option has been the most requested, according to Apple senior director Stacey Lysik.

Deal of the week

money the station

Amazoooooxxxxx. Zamazon? It’s a thing now. In case you missed it, Amazon acquired Zoox.

There have been rumors, speculation and reports about the fate of self-driving vehicle startup for months now. The WSJ had the first report in May that Amazon was in talks to acquire the self-driving company.

The official announcement, which was issued Friday morning, didn’t reveal much about the terms of the deal except that Zoox CEO Aicha Evans and co-founder and CTO Jesse Levinson will continue to lead Zoox as a standalone business.

As you might expect, there was nary a financial figure in sight. The Financial Times put the deal at $1.2 billion and The Information pegged it at “more than $1 billion.” Either way, the acquisition price was well below the $3.2 billion valuation Zoox had achieved two years before.

It wasn’t a secret that Zoox was struggling to raise a large enough round. As I’ve stated numerous times before, Zoox has the kind of ambitions that require a mountain of capital. And by mountain, I mean far north of $1 billion. The company isn’t just building the full self-driving stack — essentially the suite of hardware and software that replaces a human driver. It took on the design and development of a new bidirectional electric vehicle with no steering wheel  and it plans to operate a ride-hailing service as well.

The upshot: Zoox didn’t have a lot of options. Many automakers, Tier 1 suppliers and tech companies had already formed their various alliances and partnerships, leaving Zoox on its own. Amazon certainly has the resources to help it hit its lofty goals. That is, IF Amazon doesn’t change those goals for Zoox. For now, Amazon is publicly sticking to Zoox’ mission to build and operate a fleet of robotaxis.

And we can expect more Amazon flexing in the transportation industry. The e-commerce announced this week a $2 billion Climate Pledge Fund to invest in sustainable technologies and services that will help the company reach its commitment to be net-zero carbon in its operations by 2040. Some of that coin will go towards automation and transportation.

amazon zoox

Other deals that got our attention ….

Self-driving truck startup TuSimple has hired investment bank Morgan Stanley to help it raise $250 million, multiple sources told me. Morgan Stanley recently sent potential investors an informational packet, which I also viewed, that provides a snapshot of the company and an overview of its business model, as well as a pitch on why the company is poised to succeed. TuSimple has raised about $298 million with a valuation of more than $1 billion. Its backers include Sina, operator of China’s biggest microblogging site Weibo, Hong Kong-based investment firm Composite Capital, Nvidia, UPS, CDH Investments, Lavender Capital and Tier 1 supplier Mando Corporation.

ADAM CogTech, an Israeli automotive software startup, raised $2 million from Mobilion Ventures, the company said. Mobilion is an early-stage fund that invests in smart mobility, focusing on Israeli and global after-market innovation.

Amazon’s $575 million investment into UK food delivery startup Deliveroo has been cleared by the country’s competition regulator. The investment, which was announced more than a year ago, gave Amazon a 16% stake in Deliveroo. Now that CMA has provisionally cleared the deal, it is open for public comments until July 10. A final decision is expected August 6.

Cazoo, the British online used car marketplace, raised £25 million at a valuation in excess of $1 billion. Draper Esprit joined existing investors in the round, a group that includes DMG Ventures and General Catalyst. Cazoo has raised more than £200 million to date.

DriveU.auto, an Israeli startup that spun out of video transmission technology company LiveU, came out of stealth with $4 million in new funding. The startup has developed a connectivity platform for teleoperations. The funding round was led by RAD group co-founder Zohar Zisapel and included participation from Two Lanterns Venture Partners, Yigal Jacoby, Kaedan Capital and other private investors. Francisco Partners is an existing shareholder.

Lucid Motors gave up majority ownership to Saudi Arabia’s sovereign wealth fund in exchange for the $1.3 billion investment it closed last year, according to information disclosed in a new lawsuit, the Verge reported. Wired Middle East previously reported the PIF had taken a 67% stake. However, this is the first time an acknowledgment from the company has been made public.

Shift Technologies, an online used car marketplace, is in talks to merge with blank-check company Insurance Acquisition Corp., Bloomberg reported. Shift is aiming to be valued at more than $500 million in the deal.

Third Wave Automation, a startup developing autonomous forklift technology, emerged from stealth with $15 million in equity financing, VentureBeat reported.

Volkswagen is in talks to buy Europcar Mobility Group, the French car rental company that has a market capitalization of 390 million euros ($441 million) and net debt as of more than 1 billion euros, Reuters reported.

Truckin’

the station semi truck

Trucks have popped up a lot this week, so I figured, heck let’s dig in a bit. The big trendy discussion is about how robotaxis are OUT and autonomous Class 8 trucks are IN. This move towards trucking has actually been happening for awhile now.

The niche subcategory in the autonomous vehicle industry was rather empty in 2015 when TuSimple was founded. Then self-driving truck startup Otto came along. Uber’s 2016 acquisition of Otto certainly brought some attention to the sector. But a number of other startups had also thrown their respective hats into the trucking ring, including Embark and the now defunct Starsky Robotics. Today, this sub-industry includes Ike, Kodiak Robotics and Waymo .

This week, Amazon-backed Aurora received some press for its “shift” to trucking based off of an interview with co-founder Sterling Anderson during The Information’s Autonomous Vehicle Summit.

Let’s be clear, the company has been publicly talking about trucks since at least October 2019. The notable bit is that Anderson shared more about its work with trucks and was clearly bullish on the potential in the marketplace. Together, his comments suggest that the company is prioritizing the development of autonomous trucks over cars.

But the company designed a full self-driving stack meant to have a variety of applications, not just passenger cars. In a tweet after the interview, Anderson summarized its whole approach.

We’re compelled by a product path that goes from middle mile to last mile to mobility services.

If you can swing this technically, it allows for an elegant transition from the largest market (today) with the best unit economics and lowest level of service requirements to smaller, but rapidly growing markets with more challenging unit economics and level of service needs”

In other truckin’ news …

The California Air Resources Board adopted a new rule to phase out the most polluting vehicles on the road today. The rule will require truck manufacturers to transition from diesel trucks and vans to electric zero-emission trucks beginning in 2024. By 2045, every new truck sold in California will be zero-emission.

Russian-Finnish company Zyfra is using 5G technology to replace Wi-Fi/mesh networks used for autonomous mining dump trucks, CNET’s Roadshow reports.

Notable reads and other tidbits

AVs, ride-hailing, electric vehicles and more!

Autonomous vehicles …

Didi Chuxing said Saturday (today) that its on-demand robotaxi service will start picking up riders in Shanghai, China. Passengers may start requesting on-demand rides for free on autonomous vehicles within a designated open-traffic area that covers Shanghai’s Automobile Exhibition Center, the local business districts, subway stations and hotels in downtown Shanghai, the company said in a press release.

Lyft is using data collected from drivers on its ride-hailing app to accelerate the development of self-driving cars. Lyft’s Level 5 self-driving car program is using the data to build 3D maps, understand human driving patterns and improve simulation tests. The program is taking data from select vehicles in its Express Drive program, which provides rental cars and SUVs to drivers on its platform as an alternative to options like long-term leasing

Waymo and Volvo Car Group announced Thursday an “exclusive” partnership to integrate Waymo’s self-driving software into a new electric vehicle designed for ride-hailing. Not a ton of detail about the deal or what “exclusive” means. We know that Volvo and Uber still have a partnership. The deal with Waymo involves integrating its self-driving stack into an “all-new mobility-focused electric vehicle platform for ride hailing services.”  The partnership also includes other subsidiaries under Volvo Car Group, including electric performance brand Polestar and Lynk & Co. International, a point that Volvo Car Group CTO Henrik Green specifically noted in his prepared statement.

Mercedes-Benz and Nvidia announced a partnership to bring “software-defined” vehicles to market. The automaker’s next-generation vehicles will have a software-centric computing architecture based on Nvidia’s Drive AGX Orin computer system-on-a-chip. The underlying architecture will be standard in Mercedes vehicles, starting sometime toward the end of 2024.

It’s electric …

Apple has added a routing feature to Maps that’s designed for electric vehicle owners. The EV routing feature, which will be available in the newest version of iOS, will show charging stations compatible to a user’s electric vehicle along their route. TechCrunch’s Romain Dillet got a bit more information on this feature. He tells me that users will be able to enter their car model in the app, which will provide stops. The user can tap on the stops to see if the charging station is free or not. On sidenote, Apple is also releasing a feature that will prompt you to raise your phone and scan buildings across the street to refine your location. This feature is based on Look Around, a Google Street View-inspired feature that lets you look around as if you were walking down the street.

Arrival revealed a zero-emission bus, the next step in the company to become a major electric transportation company, the Verge reported.

Ars Technica digs into one Ohio city’s plan to get more people to buy electric cars. Hint: it worked.

Lordstown Motors unveiled an electric pickup truck prototype with four in-wheel hub motors and a few other features all aimed squarely at attracting contractors and other buyers in the commercial market. The Ohio startup didn’t get too deep into the details about the electric pickup truck known as Endurance. But we know a few more bits such as a $52,500 base price and some partnerships.

Tesla CEO Elon Musk said on Twitter that September 15 is the “tentative date” for the “Tesla Shareholder Meeting & Battery Day,” which will include the usual shareholder meeting as well as a tour of the automaker’s cell production system for the batteries that provide the power for its vehicles.

Speaking of Tesla … the National Highway Traffic Safety Administration has opened a preliminary investigation into allegations of failing touchscreens on Tesla’s older Model S vehicles.

Ride-hailing …

Lyft has agreed to settle a lawsuit from the U.S. Department of Justice that alleges the ridesharing company discriminated against disabled people — specifically those who use foldable wheelchairs or walkers.

Miscellaneous …

Alphabet’s Sidewalk Labs plans to spin out some of its smart city ideas into separate companies focused on mass timber construction, affordable electrification and planning tools optimized with machine learning and computation design, CEO Daniel Doctoroff said at Collision from Home conference, VentureBeat reported.

Ford’s Michigan Central is collaborating with Brooklyn-based Newlab to launch two “Innovation Studios” focused on solving complex transportation industry problems related to connectivity, autonomy and electrification. A corporate studio sponsored by Ford will kick off this summer to address macro mobility issues. A second civic studio will follow focusing on more immediate mobility issues in the neighborhoods around Michigan Central Station. In 2018, Ford acquired 1.2 million square feet in Corktown, Detroit’s oldest neighborhood, including the historic Michigan Central Station, with plans to establish a new mobility innovation district called Michigan Central. The first work spaces are expected to open within Michigan Central in 2022.

GM turned to 3D printing for a C8 Corvette prototype. In the end, 75% of the vehicle was 3D printed, Car and Driver reported.

See ya’ll next week!

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Tim O’Reilly has a financial incentive to pooh-pooh the traditional VC model, wherein investors gamble on nascent startups in hopes of seeing many times their money back. Bryce Roberts, who is O’Reilly’s longtime investing partner at the early-stage venture firm O’Reilly AlphaTech Ventures (OATV), now actively steers the partnership away from these riskier investments and into companies around the country that are already generating revenue and don’t necessarily want to be blitzscaled.

Yet in an interview with O’Reilly last week, he nonetheless argued persuasively for why venture capital, in its current iteration, has begun to make less sense for more founders who genuinely want to build sustainable businesses. The way he sees it, the venture industry is no longer as focused on finding small companies that might one day change the world but more on creating financial instruments for the wealthy — and that shift has real consequences.

Below, we’re pulling out parts of that conversation that may be of interest to readers who are either debating raising venture capital, debating raising more venture capital, and even those who have been turned away from VCs and perhaps dodged a bullet in the process. At a minimum, O’Reilly — who bootstrapped his own company, O’Reilly Media, 42 years ago and says it now produces “a couple hundred million dollars in revenue” yearly — provides a lot of food for thought.

TechCrunch: A lot of companies celebrated Juneteenth this year, which is a big deal. There’s been a lot of talk about making the venture industry more inclusive. How far — or not — do you think we’ve come in the venture industry on this front?

Tim O’Reilly: The thing that I would say about VC and about really everything in tech is, this concept of structural racism [is really the problem]. People think that all it matters is, ‘Well, my values are good, my heart’s in the right place, I donate to charities,’ and we don’t actually fix the systems that cause the problems.

With VCs, the networks from which they’re drawing entrepreneurs are not that different [than they have been historically]. But more importantly, the goals of the VC model are not that different. The industry sets a goal, and it has a certain kind of financial shape, which is inherently exclusionary.

How so?

The typical VC model is looking for this high-growth company with exit potential, because it’s looking for this big financial return from an IPO or acquisition, and that selects for a certain type of founder. My partner Bryce decided two funds ago [to] look for companies that are kind of disparaged as lifestyle companies that are trying to build sustainable businesses with cash flow and profits. They’re the kind of small businesses, and small business entrepreneurs, that have vanished from America, partly because of the VC myth, which is really about creating financial instruments for the wealthy.

He came up with a version of a SAFE note that allows the founders to buy out the VC at a predetermined amount if they ever become sufficiently profitable, but also gives them the optionality, because periodically, some of them do end up becoming a rocket ship. But the founder is not on the treadmill of: You have to get out.

When you start saying, ‘Okay, we’re going to look for sustainable businesses,’ you look all over the country, and Bryce ended up [with a portfolio] that’s made up of more than 50% women founders and 30% people of color, and it has been an incredible investment strategy.

That’s not to say that people who are African American or women can’t also lead companies that are part of the high-growth VC model that’s typical of Silicon Valley.

No, of course not. Of course they could lead. The talent pool is just much greater [when you look outside of Silicon Valley]. There’s a certain kind of bro culture in Silicon Valley and if you don’t fit in, sure [you could find a way], but there are a lot of impediments. That’s what we mean by structural racism.

To your point about insular networks, a prominent Black VC, Charles Hudson, has noted that a lot of [traditional VCs] just don’t have regular or professional associations with Black people, which hampers how they find companies. How has Bryce fostered some of these connections? Because it does feel like traditional VCs are right now trying to figure out how to better do this.

It’s breaking the geographic isolationism of Silicon Valley. It’s breaking the business model isolationism of Silicon Valley that says: Only things that fit this particular profile are worth investing in. Bryce didn’t go out there and say, ‘I want to go find people of color to invest in.’ What he said was, ‘I want to have a different kind of investment in different places in the United States.’ And when he did that, he naturally found entrepreneurs who reflect the diversity of America.

That’s what we have to really think about. It’s not: How do we get more Black and brown founders into this broken Silicon Valley model? It’s: How do we go figure out what the opportunities are helping them to grow businesses in their communities?

Are LPs interested in this kind of model? Does it have the kind of growth potential that they need to service their endowments?

It was a bit of a struggle when we did fund four, which was focused on [this newer model]. It was about a third of the size of fund three. But for fund five, the fundraising is [going] like gangbusters. Everybody wants in because the model has proven itself.

I don’t want to name names, but there are two companies [in the portfolio] that are kind of in similar businesses. One was in our third fund and was sort of a traditional Silicon Valley-style investment. And the other was an investment in Idaho, of all places. The first company, which involved a more traditional seed round, we’ve ended up putting in $2.5 million for a 25% stake. The one in Idaho we put in $500,000 for a 25% stake, and the one in Idaho is now twice the size of the Silicon Valley one and growing much faster.

So from what you’re seeing, the returns are actually going to be better than with a traditional Silicon Valley venture [approach].

As I said, I’ve been really disillusioned with Silicon Valley investing for a long time. It reminds me of Wall Street going up to 2008. The idea was, ‘As long as someone wants to buy this [collateralized debt obligation], we’re good.’ Nobody is thinking about: Is this a good product?

So many things that VCs have created are really financial instruments like those CDOs. They aren’t really thinking about whether this is a company that could survive on revenue from its customers. Deals are designed entirely around an exit. As long as you can get some sucker to take them, [you’re good]. So many acquisitions fail, for example, but the VCs are happy because — guess what? — they got their exit.

But now, because funds are raised so quickly, VCs have to show much more traction, which is where things like blitzscaling come in.

Just the way you’re describing it. Can’t you hear what’s wrong with that? It’s for the benefit of the VCs, the VCs have to show, not the entrepreneurs have to show.

Aren’t the LPs addicted to that crack? Don’t they want to see that quick financial traction?

Yeah, but you know that VC returns have actually lagged public markets for four decades now. It’s a little bit like the lottery. The only sure winners are the VCs because the VCs who don’t return their fund get their management fees every year.

A huge amount of the VC capital doesn’t return. Everybody just sees the really big wins. And I know when they happen, it’s really wonderful. But I think [those rare wins] have gotten an outsize place, and they’ve displaced other kinds of investment. It’s part of the structural inequality in our society, where we’re building businesses that are optimized for their financial return rather than their return to society.

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Tim O’Reilly has a financial incentive to pooh-pooh the traditional VC model, wherein investors gamble on nascent startups in hopes of seeing many times their money back. Bryce Roberts, who is O’Reilly’s longtime investing partner at the early-stage venture firm O’Reilly AlphaTech Ventures (OATV), now actively steers the partnership away from these riskier investments and into companies around the country that are already generating revenue and don’t necessarily want to be blitzscaled.

Yet in an interview with O’Reilly last week, he nonetheless argued persuasively for why venture capital, in its current iteration, has begun to make less sense for more founders who genuinely want to build sustainable businesses. The way he sees it, the venture industry is no longer as focused on finding small companies that might one day change the world but more on creating financial instruments for the wealthy — and that shift has real consequences.

Below, we’re pulling out parts of that conversation that may be of interest to readers who are either debating raising venture capital, debating raising more venture capital, and even those who have been turned away from VCs and perhaps dodged a bullet in the process. At a minimum, O’Reilly — who bootstrapped his own company, O’Reilly Media, 42 years ago and says it now produces “a couple hundred million dollars in revenue” yearly — provides a lot of food for thought.

TechCrunch: A lot of companies celebrated Juneteenth this year, which is a big deal. There’s been a lot of talk about making the venture industry more inclusive. How far — or not — do you think we’ve come in the venture industry on this front?

Tim O’Reilly: The thing that I would say about VC and about really everything in tech is, this concept of structural racism [is really the problem]. People think that all it matters is, ‘Well, my values are good, my heart’s in the right place, I donate to charities,’ and we don’t actually fix the systems that cause the problems.

With VCs, the networks from which they’re drawing entrepreneurs are not that different [than they have been historically]. But more importantly, the goals of the VC model are not that different. The industry sets a goal, and it has a certain kind of financial shape, which is inherently exclusionary.

How so?

The typical VC model is looking for this high-growth company with exit potential, because it’s looking for this big financial return from an IPO or acquisition, and that selects for a certain type of founder. My partner Bryce decided two funds ago [to] look for companies that are kind of disparaged as lifestyle companies that are trying to build sustainable businesses with cash flow and profits. They’re the kind of small businesses, and small business entrepreneurs, that have vanished from America, partly because of the VC myth, which is really about creating financial instruments for the wealthy.

He came up with a version of a SAFE note that allows the founders to buy out the VC at a predetermined amount if they ever become sufficiently profitable, but also gives them the optionality, because periodically, some of them do end up becoming a rocket ship. But the founder is not on the treadmill of: You have to get out.

When you start saying, ‘Okay, we’re going to look for sustainable businesses,’ you look all over the country, and Bryce ended up [with a portfolio] that’s made up of more than 50% women founders and 30% people of color, and it has been an incredible investment strategy.

That’s not to say that people who are African American or women can’t also lead companies that are part of the high-growth VC model that’s typical of Silicon Valley.

No, of course not. Of course they could lead. The talent pool is just much greater [when you look outside of Silicon Valley]. There’s a certain kind of bro culture in Silicon Valley and if you don’t fit in, sure [you could find a way], but there are a lot of impediments. That’s what we mean by structural racism.

To your point about insular networks, a prominent Black VC, Charles Hudson, has noted that a lot of [traditional VCs] just don’t have regular or professional associations with Black people, which hampers how they find companies. How has Bryce fostered some of these connections? Because it does feel like traditional VCs are right now trying to figure out how to better do this.

It’s breaking the geographic isolationism of Silicon Valley. It’s breaking the business model isolationism of Silicon Valley that says: Only things that fit this particular profile are worth investing in. Bryce didn’t go out there and say, ‘I want to go find people of color to invest in.’ What he said was, ‘I want to have a different kind of investment in different places in the United States.’ And when he did that, he naturally found entrepreneurs who reflect the diversity of America.

That’s what we have to really think about. It’s not: How do we get more Black and brown founders into this broken Silicon Valley model? It’s: How do we go figure out what the opportunities are helping them to grow businesses in their communities?

Are LPs interested in this kind of model? Does it have the kind of growth potential that they need to service their endowments?

It was a bit of a struggle when we did fund four, which was focused on [this newer model]. It was about a third of the size of fund three. But for fund five, the fundraising is [going] like gangbusters. Everybody wants in because the model has proven itself.

I don’t want to name names, but there are two companies [in the portfolio] that are kind of in similar businesses. One was in our third fund and was sort of a traditional Silicon Valley-style investment. And the other was an investment in Idaho, of all places. The first company, which involved a more traditional seed round, we’ve ended up putting in $2.5 million for a 25% stake. The one in Idaho we put in $500,000 for a 25% stake, and the one in Idaho is now twice the size of the Silicon Valley one and growing much faster.

So from what you’re seeing, the returns are actually going to be better than with a traditional Silicon Valley venture [approach].

As I said, I’ve been really disillusioned with Silicon Valley investing for a long time. It reminds me of Wall Street going up to 2008. The idea was, ‘As long as someone wants to buy this [collateralized debt obligation], we’re good.’ Nobody is thinking about: Is this a good product?

So many things that VCs have created are really financial instruments like those CDOs. They aren’t really thinking about whether this is a company that could survive on revenue from its customers. Deals are designed entirely around an exit. As long as you can get some sucker to take them, [you’re good]. So many acquisitions fail, for example, but the VCs are happy because — guess what? — they got their exit.

But now, because funds are raised so quickly, VCs have to show much more traction, which is where things like blitzscaling come in.

Just the way you’re describing it. Can’t you hear what’s wrong with that? It’s for the benefit of the VCs, the VCs have to show, not the entrepreneurs have to show.

Aren’t the LPs addicted to that crack? Don’t they want to see that quick financial traction?

Yeah, but you know that VC returns have actually lagged public markets for four decades now. It’s a little bit like the lottery. The only sure winners are the VCs because the VCs who don’t return their fund get their management fees every year.

A huge amount of the VC capital doesn’t return. Everybody just sees the really big wins. And I know when they happen, it’s really wonderful. But I think [those rare wins] have gotten an outsize place, and they’ve displaced other kinds of investment. It’s part of the structural inequality in our society, where we’re building businesses that are optimized for their financial return rather than their return to society.

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